Went to clear and recreate the report schedule and set it to e-mail us, and we got this awesome non-descript error ID: 3014. "An error occurred causing the reporting job on
I checked out the guide and the basic idea to "repair" is uninstall and reinstall. I don't know about you all, but risking loosing backup data just to fix reporting didn't sit well. So, I proceeded to evaluate what was occurring with the SQL Server Profiler on our system and comparing it to our secondary server.
After playing around with it for hours, seemed to narrow down that it was an issue with permissions for the Reporting Services predefined database role called RSExecRole. I went through this guide Create the RSExecRole (http://technet.microsoft.com/en-us/library/cc281308.aspx), used to recreate permissions during a report database move, and we were able to recreate the e-mail subscriptions. It looks like there must have been some undetected failure during the SP1 upgrade.